Water → HCID 117843756, compound

HRID 2209055Notes

Reaction equation

HRID 2209055 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:21]2[N:26]=[C:25](S(C)(=O)=O)[C:24]3[N:31]([CH3:34])[CH:32]=[N:33][C:23]=3[CH:22]=2)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].[OH2:35].CCO[C:39]([CH3:41])=[O:40]>CN(C=O)C>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:21]2[N:26]=[C:25]([O:35][C@H:23]([C@H:24]3[CH2:25][NH:26][C:39](=[O:40])[CH2:41]3)[CH3:22])[C:24]3[N:31]([CH3:34])[CH:32]=[N:33][C:23]=3[CH:22]=2)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 117843001HCID 117843001, compound

Product 1

HCID 117843756HCID 117843756, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of alcohol (1.0-1.2 eq) in DMF was added NaHMDS (1.0M in THF, 1.3 eq), and the reaction was stirred for 15 min. 2.41 or 2.65 (1.0 eq) was added and the reaction was stirred at RT for 2 hours. Water and EtOAc were added, the layers separated, and the aqueous layer was extracted with EtOAc, and the combined organics were dried, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. The isolated material was transferred to sealable vial, TFA was added and the reaction was heated to 60° C. for 12-18 hours. The reaction was concentrated and the residue was purified by RP-HPLC to yield Examples 3D.01-3D.09.

Workup

  1. stirringthe reaction was stirred at RT for 2 hours
  2. customthe layers separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. customthe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. additionwas added
  9. concentrationThe reaction was concentrated
  10. customthe residue was purified by RP-HPLC
  11. customto yield Examples 3D.01-3D.09

Sources & evidence

ORD record
ord-90299a44a90e43c6a5535a92abab8972
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

Loading…